Skip to main content
SpringerLink
Log in

The chemical synthesis of sterols: Latest advances

  • Published:
Chemistry of Natural Compounds Aims and scope

Abstract

This review discusses the results of investigations on the chemical synthesis of sterols during 1981–1996.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. G. B. Elikov and V. A. Stonik,The Steroids of Marine Organisms [in Russian], Nauka, Moscow (1988).

    Google Scholar 

  2. N. V. Kovganko and A. A. Akhrem,Steroids: Ecological Functions [in Russian], Nauka i Tekhnika, Minsk (1990).

    Google Scholar 

  3. D. M. Piatak and J. Wicha,Chem. Rev.,78, No. 3, 199 (1978).

    Google Scholar 

  4. J. Redpath and F. J. Zeelen,Chem. Soc. Rev.,12, No. 1 75 (1983).

    Google Scholar 

  5. V. N. Zhabinskii, V. K. Ol'khovik, and V. A. Khripach,Zh. Org. Khim.,32, No. 3, 327 (1996).

    Google Scholar 

  6. N. Schmuff and B. M. Trost,J. Org. Chem.,48, No. 9. 1404 (1983).

    Google Scholar 

  7. M. Ohmori, S. Yamada, H. Takayama, and K. Ochi,Tetrahedron Lett.,23, No. 45, 4709 (1982).

    Google Scholar 

  8. J. P. Marino and H. Abe,J. Am. Chem. Soc.,103, No. 10, 2907 (1981).

    Google Scholar 

  9. H. W. Kircher and F. U. Rosenstein,J. Org. Chem.,47, No. 9, 1722 (1982).

    Google Scholar 

  10. H. W. Kircher and F. U. Rosenstein,J. Org. Chem.,52, No. 12, 2586 (1987).

    Google Scholar 

  11. S. Takano, S. Yamada, H. Numata, and K. Ogasawara,J. Chem. Soc., Chem. Commun., No. 14, 760 (1983).

    Google Scholar 

  12. K. Maruoka, R. Bureau, and H. Yamamoto,Synlett.,5, 363 (1991).

    Google Scholar 

  13. J. M. Joseph and W. R. Nes,J. Chem. Soc., Chem. Commun., No. 8, 367 (1981).

    Google Scholar 

  14. R. E. Dolle, S. J. Schmidt, and L. I. Cruse,J. Chem. Soc., Chem. Commun., No. 1, 19 (1988).

    Google Scholar 

  15. N. Ogihara and M. Morisaki,Chem. Pharm. Bull.,36, No. 7, 2724 (1988).

    Google Scholar 

  16. F. Dolle, C. Kappler, C. Hetru, B. Rousseau, M. Coppo, B. Luu, and J. A. Hoffmann,Tetrahedron,46, No. 15, 5305 (1990).

    Google Scholar 

  17. M. Anastasia, A. Fiecchi, and G. Galli,J. Org. Chem.,46, 3421 (1981).

    Google Scholar 

  18. K. Schonauer and E. Zbiral,Osterr. Chem. Z.,84, No. 9, 231 (1983).

    Google Scholar 

  19. T. Ibuka, T. Taga, S. Nishii, and Y. Yamamoto,J. Chem. Soc., Chem. Commun., No. 5, 342 (1988).

    Google Scholar 

  20. T. Ibuka, T. Taga, T. Shingu, M. Saito, S. Nishii, and Y. Yamamoto,J. Org. Chem.,53, No. 17, 3947 (1988).

    Google Scholar 

  21. L. S. Stevovic, V. Soskic, and I. O. Juranic,J. Serb. Chem. Soc.,60, No. 12, 1071 (1995).

    Google Scholar 

  22. H. Suginome, H. Senboku, and S. Yamada,J. Chem. Soc., Perkin Trans. I, No. 8, 2199 (1990).

    Google Scholar 

  23. M. Anastasia, P. Ciuffreda, and A. Fiecchi,J. Chem. Soc., Perkin Trans. I, No. 2, 379 (1983).

    Google Scholar 

  24. M. Anastasia, P. Allevi, P. Ciuffreda, A. Fiecchi, and A. Scala,J. Org. Chem.,49, No. 22, 4297 (1984).

    Google Scholar 

  25. P. Allevi, M. Anastasia, R. Cerana, P. Ciuffreda, and P. Lado,Phytochemistry,27, No. 5, 1309 (1988).

    Google Scholar 

  26. A. A. Akhrem, V. A. Khripach, V. N. Zhabinskii, and V. K. Ol'khovik,Vestsi Akad. Navuk BSSR, Ser. Khim. Navuk, No. 2, 69 (1989).

    Google Scholar 

  27. D. H. R. Barton, X. Lusinchi, L. Magdzinski, and J. S. Ramirez,J. Chem. Soc., Chem. Commun., No. 18, 1236 (1984).

    Google Scholar 

  28. V. A. Khripach, V. N. Zhabinskii, and E. V. Zhernosek,Vestsi Akad. Navuk BSSR, Ser. Khim. Navuk, No. 6, 84 (1991).

    Google Scholar 

  29. V. A. Khripach, V. N. Zhabinskii, E. V. Zhernosek, and F. A. Lakhvich,USSR Inventors' Certificate No. 1594181 (1990).Byull. Izob., No. 35, 132 (1990).

    Google Scholar 

  30. V. A. Khripach, V. N. Zhabinskii, and E. V. Zhernosek,Khim. Prir. Soedin., 90 (1992).

  31. M. Anastasia and A. Fiecchi,J. Chem. Soc., Perkin Trans. I, 2125 (1981).

  32. W. C. Dow, T. Gebreyesus, S. Popov, R. M. K. Carlson, and C. Djerassi,Steroids,42, 217 (1983).

    Google Scholar 

  33. M. Anastasia, P. Allevi, P. Ciuffreda, and A. Fiecchi,J. Chem. Soc., Perkin Trans. I, 2365 (1983).

  34. Y. Fujimoto, M. Kimura, F. A. M. Khalifa, and N. Ikekawa,Chem. Pharm. Bull.,32, 4372 (1984).

    Google Scholar 

  35. M. Anastasia, P. Ciuffreda, M. Del Puppo, and A. Fiecchi,J. Chem. Soc., Perkin Trans. I, 383 (1983).

  36. W.-S. Zhou, L.-Q. Sun, and X.-F. Pan,Acta Chim. Sin.,50, 1192 (1992).

    Google Scholar 

  37. R. W. Lang and C. Djerassi,J. Org. Chem.,47, 625 (1982).

    Google Scholar 

  38. R. W. Lang and C. Djerassi,Helv. Chim. Acta,65, 407 (1982).

    Google Scholar 

  39. M. Anastasia and A. Fiecchi,J. Org. Chem.,46, 1726 (1981).

    Google Scholar 

  40. T. Gebreyesus, I. Stollov, F.-T. Luo, and C. Djerassi,Steroids,45, 447 (1985).

    Google Scholar 

  41. C. A. N. Catalan, W. C. M. C. Kokke, C. Duque, and C. Djerassi,J. Org. Chem.,48, 5207 (1983).

    Google Scholar 

  42. Y. Hirano and C. Djerassi,J. Org. Chem.,47, 2420 (1982).

    Google Scholar 

  43. Y. Fujimoto, M. Kimura, T. Terasawa, F. A. M. Khalifa, and N. Ikekawa,Tetrahedron Lett.,25, 1805 (1984).

    Google Scholar 

  44. T. Itoh, D. Sica, and C. Djerassi,J. Chem. Soc., Perkin Trans. I, 147 (1983).

  45. A. Y. L. Shu and C. Djerassi,Tetrahedron Lett.,22, 4627 (1981).

    Google Scholar 

  46. L. L. Niang, U. Sjostrand, and C. Djerassi,J. Am. Chem. Soc.,103, 115 (1981).

    Google Scholar 

  47. T. G. Back, J. R. Proudfoot, and C. Djerassi,Tetrahedron Lett.,27, 2187 (1986).

    Google Scholar 

  48. L. N. Li, U. Sjostrand, and C. Djerassi,J. Org. Chem.,46, 3867 (1981).

    Google Scholar 

  49. J. Zielinski, H. Li, T. S. Milkova, S. Popov, N. L. Marekov, and C. Djerassi,Tetrahedron Lett.,22, 2345 (1981).

    Google Scholar 

  50. I. L. Stollov, J. E. Thompson, J.-H. Cho, and C. Djerassi,J. Am. Chem. Soc.,108, 8235 (1986).

    Google Scholar 

  51. B. V. Crist, X. Li, P. R. Bergquist, and C. Djerassi,J. Org. Chem.,48, 4472 (1983).

    Google Scholar 

  52. J.-H. Cho and C. Djerassi,J. Org. Chem.,52, 4517 (1987).

    Google Scholar 

  53. L. N. Li and C. Djerassi,J. Am. Chem. Soc.,103, 3606 (1981).

    Google Scholar 

  54. X. Li and C. Djerassi,Tetrahedron Lett.,24, 665 (1983).

    Google Scholar 

  55. R. W. Lang and C. Djerassi,J. Org. Chem.,47, 625 (1982).

    Google Scholar 

  56. D. Kim,Arch. Pharm. Res.,15, 374 (1992).

    Google Scholar 

  57. S. Sato, A. Akaiwa, Y. Fujimoto, M. Ishiguro, and N. Ikekawa,Chem. Pharm. Bull.,29, 406 (1981).

    Google Scholar 

  58. T. Terasawa, Y. Hirano, Y. Fujimoto, and N. Ikekawa,J. Chem. Soc., Chem. Commun., 1180 (1983).

  59. J. R. Proudfoot and C. Djerassi,Tetrahedron Lett.,25, 5493 (1984).

    Google Scholar 

  60. Y. Fujimoto, M. Kimura, T. Terasawa, F. A. M. Khalifa, and N. Ikekawa,Tetrahedron Lett.,25, 1805 (1984).

    Google Scholar 

  61. J. P. Genet, F. Colobert, and J. M. Gaudin, in:International Conference on Organic Synthesis, Moscow (1986), p. 167.

  62. C. Bonini, R. B. Kinnel, P. J. Scheuer, and C. Djerassi,Tetrahedron Lett.,24, 277 (1983).

    Google Scholar 

  63. C. A. N. Catalan and C. Djerassi,Tetrahedron Lett.,24, 3461 (1983).

    Google Scholar 

  64. C. J. Silva, J.-L. Giner, and C. Djerassi,J. Am. Chem. Soc.,114, 295 (1992).

    Google Scholar 

  65. T. Honda, M. Katoh, and S. Yamane,J. Chem. Soc., Perkin Trans. I, 2291 (1996).

  66. J. R. Proudfoot and C. Djerassi,J. Am. Chem. Soc.,106, 5613 (1984).

    Google Scholar 

  67. Y. Fujimoto, M. Ohhana, T. Terasawa, and N. Ikekawa,Tetrahedron Lett.,26, 3239 (1985).

    Google Scholar 

  68. T. B. Tam Ha and C. Djerassi,Tetrahedron Lett.,26, 4031 (1985).

    Google Scholar 

  69. J. R. Proudfoot, X. Li, and C. Djerassi,J. Org. Chem.,50, 2026 (1985).

    Google Scholar 

  70. A. Kurek-Tyrlik, K. Minksztym, and J. Wicha,J. Am. Chem. Soc.,117, 1849 (1995).

    Google Scholar 

Download references

Authors
  1. N. V. Kovganko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. K. Ananich
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus', 220141, Belarus', Minsk, Ul. Zhodinskaya, 5/2. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 257–290, May–June, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kovganko, N.V., Ananich, S.K. The chemical synthesis of sterols: Latest advances. Chem Nat Compd 35, 229–259 (1999). https://doi.org/10.1007/BF02234845

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02234845

Keywords

Search

Navigation